Enzyme-like C-H Oxidation of Glucosides Promoted by Visible Light

Abstract

To match nature's prowess at using enzymes to make desired motifs in a regioselective fashion, we explore the use of visible light for the selective oxidation of the hydroxyl group to afford the corresponding ketosaccharide. This highly admirable approach offers several advantages over the enzymatic approach in terms of yields and the scope of substrates. Herein, we report the development of a simple visiblelight- promoted selective oxidation of unprotected glucosides that allows for inexpensive access to valuable keto-saccharide building blocks. The method is employed on a variety of different natural and artificial glucosides, is operationally simple and scalable, and can be used to access keto-saccharides rapidly and inexpensively.